methyl 2-[4-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)cyclohexyl]acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-[4-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)cyclohexyl]acetate
• 英文别名: Methyl 2-[4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)cyclohexyl]acetate；methyl 2-[4-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)cyclohexyl]acetate
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: AWTOKMQKKBCYST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-[4-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)cyclohexyl]acetate 在 2,4,6-三甲基吡啶 、 platinum(IV) oxide 、 aluminum (III) chloride 、 2,6-二叔丁基-4-甲基吡啶 、 草酰氯 、 氢气 、 copper(l) cyanide 、 lithium carbonate 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 22.17h， 生成 methyl 2-{(trans)-5′-isobutyryl-2′,3′-dihydrospiro[cyclohexane-1,1′-inden]-4-yl}acetate
  参考文献：
  名称：

  A Practical Synthesis of a Potent and Selective Diacylglycerol Acyltransferase-1 (DGAT-1) Inhibitor

  摘要：

  A practical synthesis of a potent, selective, and orally efficacious diacylglycerol acyltransferase-1 (DGAT-1) inhibitor, is described. This synthesis is suitable for multi-kilogram scale with high regioselectivity and stereoselectivity. The synthesis involves a Knoevenagel condensation with Meldrum's acid followed by the stereoselective addition of phenyl cuprate, regioselective Friedel-Crafts acylation, cyclization, and a regioselective reduction through an enol triflate with catalytic platinum oxide to provide the desired compound in 5.2% yield over 12 steps.

  DOI：

  10.1055/s-0034-1378653
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 80.58h， 生成 methyl 2-[4-(2,2-Dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)cyclohexyl]acetate
  参考文献：
  名称：

  A Practical Synthesis of a Potent and Selective Diacylglycerol Acyltransferase-1 (DGAT-1) Inhibitor

  摘要：

  A practical synthesis of a potent, selective, and orally efficacious diacylglycerol acyltransferase-1 (DGAT-1) inhibitor, is described. This synthesis is suitable for multi-kilogram scale with high regioselectivity and stereoselectivity. The synthesis involves a Knoevenagel condensation with Meldrum's acid followed by the stereoselective addition of phenyl cuprate, regioselective Friedel-Crafts acylation, cyclization, and a regioselective reduction through an enol triflate with catalytic platinum oxide to provide the desired compound in 5.2% yield over 12 steps.

  DOI：

  10.1055/s-0034-1378653